4-Amino-3-(1,2,3,4,5-penta­hydroxy­pentyl)-1,2,4-1H-triazole-5(4H)-thione

In the title compound, C₇H₁₄N₄O₅S, the 5-mercapto substituent of the 1,2,4-triazole exists in the thione form [C=S = 1.666 (5) Å], with the protonated N atom of the triazolyl ring, the amine group and the hydroxy groups of the pentyl chain engaged in extensive hydrogen-bonding interactions, giving rise to a three-dimensional network structure.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.047
• wR factor = 0.095
• Data-to-parameter ratio = 6.6

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of Tmax/Tmin expected RT(exp) is > 1.10
            Absorption corrections should be applied.
            Tmin and Tmax expected:      0.877     0.981
            RT(exp) =      1.118
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 8 for a
            non-centrosymmetric structure, where ZMAX < 18
            sine(theta)/lambda                0.6212
            Proportion of unique data used    0.8265
            Ratio reflections to parameters   6.6375
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro .          ?
PLAT057_ALERT_3_C Correction for Absorption Required   RT(exp) ...       1.12
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       6.64
PLAT127_ALERT_1_C Implicit Hall Symbol Inconsistent with Expl ....        1 p
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           26.20
           From the CIF: _reflns_number_total               1285
           Count of symmetry unique reflns         1081
           Completeness (_total/calc)            118.87%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       204
           Fraction of Friedel pairs measured     0.189
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

4-Amino-3-(1,2,3,4,5-pentahydroxylpentyl)-1,2,4–1H-triazol-5-thione

Crystal data

C7H14N4O5S	Z = 1
Mr = 266.28	F(000) = 140
Triclinic, P1	Dx = 1.637 Mg m^−3
Hall symbol: 1 P	Mo Kα radiation, λ = 0.71073 Å
a = 4.875 (1) Å	Cell parameters from 582 reflections
b = 5.306 (2) Å	θ = 3.9–24.5°
c = 10.669 (3) Å	µ = 0.32 mm^−1
α = 101.486 (4)°	T = 298 K
β = 92.884 (4)°	Plate, colorless
γ = 90.339 (4)°	0.42 × 0.35 × 0.06 mm
V = 270.1 (1) Å^3

Data collection

Bruker APEX area-detector diffractometer	1002 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 26.2°, θmin = 2.0°
φ and ω scan	h = −6→5
1583 measured reflections	k = −4→6
1285 independent reflections	l = −13→13

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0455P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.001
1062 reflections	Δρmax = 0.23 e Å^−3
160 parameters	Δρmin = −0.24 e Å^−3
3 restraints	Absolute structure: Friedel pairs were merged.
Primary atom site location: structure-invariant direct methods

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.4999 (3)	0.5004 (2)	0.49997 (15)	0.0477 (5)
O1	−0.3667 (7)	−0.1357 (7)	0.2732 (3)	0.0351 (10)
H1o	−0.2812	−0.1460	0.3401	0.042*
O2	−0.5397 (7)	−0.2940 (7)	0.0312 (4)	0.0286 (8)
H2o	−0.4568	−0.4237	0.0002	0.034*
O3	−0.0511 (7)	−0.3054 (7)	−0.0970 (4)	0.0326 (9)
H3o	0.0993	−0.3017	−0.0587	0.039*
O4	−0.5074 (7)	0.2141 (7)	−0.1276 (4)	0.0357 (10)
H4o	−0.6503	0.2148	−0.1714	0.043*
O5	−0.0081 (7)	0.2081 (7)	−0.2601 (4)	0.0345 (9)
H5o	−0.0731	0.3352	−0.2155	0.041*
N1	0.0915 (8)	0.2955 (8)	0.1707 (4)	0.0285 (10)
N2	0.2770 (9)	0.4459 (8)	0.2574 (4)	0.0318 (11)
H2a	0.3663	0.5741	0.2402	0.038*
N3	0.1284 (9)	0.1668 (7)	0.3538 (4)	0.0267 (10)
N4	0.0768 (10)	0.0201 (9)	0.4457 (4)	0.0388 (13)
H4a	0.2114	−0.0915	0.4485	0.047*
H4c	0.0682	0.1234	0.5221	0.047*
C1	0.3036 (11)	0.3726 (9)	0.3701 (5)	0.0297 (12)
C2	0.0093 (10)	0.1256 (9)	0.2331 (5)	0.0251 (11)
C3	−0.1792 (10)	−0.1019 (10)	0.1799 (5)	0.0259 (12)
H3	−0.0677	−0.2565	0.1603	0.031*
C4	−0.3529 (11)	−0.0780 (10)	0.0589 (5)	0.0255 (11)
H4	−0.4601	0.0794	0.0780	0.031*
C5	−0.1854 (10)	−0.0666 (10)	−0.0562 (5)	0.0237 (11)
H5	−0.0473	0.0720	−0.0330	0.028*
C6	−0.3667 (11)	−0.0208 (10)	−0.1701 (5)	0.0273 (12)
H6	−0.5014	−0.1620	−0.1946	0.033*
C7	−0.2080 (12)	0.0028 (10)	−0.2848 (5)	0.0352 (14)
H7a	−0.1155	−0.1579	−0.3142	0.042*
H7b	−0.3362	0.0296	−0.3533	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0550 (11)	0.0439 (9)	0.0404 (9)	−0.0133 (7)	−0.0184 (8)	0.0046 (7)
O1	0.033 (2)	0.044 (2)	0.030 (2)	−0.0169 (19)	−0.0023 (18)	0.0118 (18)
O2	0.0199 (19)	0.0308 (19)	0.032 (2)	−0.0038 (15)	−0.0038 (15)	0.0016 (16)
O3	0.025 (2)	0.036 (2)	0.034 (2)	0.0069 (17)	−0.0022 (18)	0.0006 (17)
O4	0.030 (2)	0.037 (2)	0.038 (2)	0.0037 (18)	−0.0099 (19)	0.0039 (18)
O5	0.032 (2)	0.035 (2)	0.034 (2)	−0.0016 (17)	0.0005 (17)	0.0037 (17)
N1	0.028 (3)	0.029 (2)	0.028 (2)	−0.0059 (19)	−0.0024 (19)	0.005 (2)
N2	0.033 (3)	0.027 (3)	0.036 (3)	−0.010 (2)	−0.002 (2)	0.009 (2)
N3	0.031 (3)	0.024 (2)	0.024 (2)	−0.0059 (19)	0.0008 (19)	0.0053 (19)
N4	0.049 (3)	0.040 (3)	0.029 (3)	−0.012 (2)	−0.001 (2)	0.011 (2)
C1	0.027 (3)	0.026 (3)	0.037 (3)	−0.002 (2)	0.002 (2)	0.008 (2)
C2	0.024 (3)	0.025 (3)	0.027 (3)	−0.001 (2)	0.000 (2)	0.005 (2)
C3	0.019 (3)	0.032 (3)	0.028 (3)	−0.002 (2)	0.007 (2)	0.006 (2)
C4	0.022 (3)	0.025 (3)	0.028 (3)	−0.004 (2)	−0.002 (2)	0.003 (2)
C5	0.022 (3)	0.023 (2)	0.024 (3)	0.000 (2)	−0.002 (2)	0.001 (2)
C6	0.024 (3)	0.029 (3)	0.026 (3)	−0.003 (2)	−0.004 (2)	0.000 (2)
C7	0.042 (4)	0.032 (3)	0.028 (3)	−0.010 (3)	−0.004 (3)	−0.001 (2)

Geometric parameters (Å, º)

S1—C1	1.668 (5)	C6—C7	1.505 (8)
O1—C3	1.421 (5)	O1—H1o	0.8200
O2—C4	1.434 (6)	O2—H2o	0.8200
O3—C5	1.429 (6)	O3—H3o	0.8200
O4—C6	1.430 (6)	O4—H4o	0.8200
O5—C7	1.433 (6)	O5—H5o	0.8200
N1—C2	1.295 (6)	N2—H2a	0.8600
N1—N2	1.387 (5)	N4—H4a	0.8900
N2—C1	1.336 (7)	N4—H4c	0.8900
N3—C1	1.360 (6)	C3—H3	0.9800
N3—C2	1.362 (6)	C4—H4	0.9800
N3—N4	1.399 (6)	C5—H5	0.9800
C2—C3	1.512 (7)	C6—H6	0.9800
C3—C4	1.535 (7)	C7—H7a	0.9700
C4—C5	1.519 (7)	C7—H7b	0.9700
C5—C6	1.526 (6)
C2—N1—N2	103.2 (4)	C5—O3—H3o	109.5
C1—N2—N1	113.5 (4)	C6—O4—H4o	109.5
C1—N3—C2	109.1 (4)	C7—O5—H5o	109.5
C1—N3—N4	125.9 (4)	C1—N2—H2a	123.2
C2—N3—N4	125.1 (4)	N1—N2—H2a	123.2
N2—C1—N3	102.9 (4)	N3—N4—H4a	109.5
N2—C1—S1	129.1 (4)	N3—N4—H4c	109.5
N3—C1—S1	128.0 (4)	H4a—N4—H4c	109.5
N1—C2—N3	111.3 (4)	O1—C3—H3	108.6
N1—C2—C3	125.9 (4)	C2—C3—H3	108.6
N3—C2—C3	122.7 (4)	C4—C3—H3	108.6
O1—C3—C2	109.7 (4)	O2—C4—H4	108.4
O1—C3—C4	106.6 (4)	C5—C4—H4	108.4
C2—C3—C4	114.8 (4)	C3—C4—H4	108.4
O2—C4—C5	110.6 (4)	O3—C5—H5	109.4
O2—C4—C3	107.0 (4)	C4—C5—H5	109.4
C5—C4—C3	114.0 (4)	C6—C5—H5	109.4
O3—C5—C4	110.3 (4)	O4—C6—H6	109.2
O3—C5—C6	106.8 (4)	C7—C6—H6	109.2
C4—C5—C6	111.6 (4)	C5—C6—H6	109.2
O4—C6—C7	109.1 (4)	O5—C7—H7a	108.8
O4—C6—C5	106.6 (4)	C6—C7—H7a	108.8
C7—C6—C5	113.5 (4)	O5—C7—H7b	108.8
O5—C7—C6	113.8 (4)	C6—C7—H7b	108.8
C3—O1—H1o	109.5	H7a—C7—H7b	107.7
C4—O2—H2o	109.5
C2—N1—N2—C1	−1.0 (6)	N3—C2—C3—C4	164.2 (5)
N1—N2—C1—N3	0.2 (6)	O1—C3—C4—O2	−51.8 (5)
N1—N2—C1—S1	−179.4 (4)	C2—C3—C4—O2	−173.4 (4)
C2—N3—C1—N2	0.7 (5)	O1—C3—C4—C5	−174.3 (4)
N4—N3—C1—N2	−179.1 (5)	C2—C3—C4—C5	64.1 (6)
C2—N3—C1—S1	−179.7 (4)	O2—C4—C5—O3	−54.4 (5)
N4—N3—C1—S1	0.5 (8)	C3—C4—C5—O3	66.1 (5)
N2—N1—C2—N3	1.4 (6)	O2—C4—C5—C6	64.1 (5)
N2—N1—C2—C3	−174.7 (5)	C3—C4—C5—C6	−175.3 (4)
C1—N3—C2—N1	−1.4 (6)	O3—C5—C6—O4	178.1 (4)
N4—N3—C2—N1	178.4 (5)	C4—C5—C6—O4	57.6 (5)
C1—N3—C2—C3	174.9 (5)	O3—C5—C6—C7	−61.8 (5)
N4—N3—C2—C3	−5.3 (8)	C4—C5—C6—C7	177.6 (4)
N1—C2—C3—O1	−140.0 (5)	O4—C6—C7—O5	59.5 (6)
N3—C2—C3—O1	44.2 (7)	C5—C6—C7—O5	−59.1 (6)
N1—C2—C3—C4	−20.1 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N4	0.82	2.12	2.778 (6)	138
O2—H2o···O4^i	0.82	2.13	2.824 (5)	143
O3—H3o···O2^ii	0.82	1.96	2.777 (5)	179
O4—H4o···O5^iii	0.82	1.94	2.755 (5)	174
O5—H5o···O3^iv	0.82	2.07	2.827 (5)	154
N2—H2a···O1^v	0.86	1.98	2.784 (5)	156
N4—H4c···O5^vi	0.89	2.33	3.147 (6)	153
N4—H4a···S1^i	0.89	2.72	3.574 (5)	161

Symmetry codes: (i) x, y−1, z; (ii) x+1, y, z; (iii) x−1, y, z; (iv) x, y+1, z; (v) x+1, y+1, z; (vi) x, y, z+1.